Italy, what can I say? It’s a truly magical place! My pictures don’t do it justice. From the food to the history, it was an amazing trip, and we will be back!

Here is how we spent 10 days in Italy.


Day 1: Travel & Tuscany Arrival

We left the Indy airport at 2:50pm and had a short connection in Dulles. Then we were off to Rome, where we landed the next morning at 8:00am. We flew United and they were great. So many meals, snacks and movies : ) Once we arrived in Rome we found our ground transportation and it was almost a 3 hour ride to where we were staying in Tuscany, which was not fun for this 7 week pregnant lady.

Hotel: Castel Monastero 

Hotel Room

Hotel Room

View From Our Room

I would stay here again! The rooms were wonderful, romantic. The pool, spa, food, everything was top notch. It was also a good central location for exploring different cities in Tuscany. That being said, it was very isolated. By that I mean, you couldn’t walk to any shops, restaurants, etc. or even take a 5-10 minute ride to any.

We arrived at the resort, checked in and rested up a bit. Then that evening we had a welcome reception and dinner with Ryan’s co-workers at our hotel. The restaurant and food was amazing! I hear the wine was too.

Dinner At The Hotel


Day 2: Montepulciano & Montalcino

We woke up and had breakfast at the hotel. A huge spread full of meats, cheeses, and pastries was set up every morning. It never sounded great to me, but Ryan liked it, and I’m sure I would if I didn’t feel so nauseous. Also I don’t drink coffee, just a black iced tea in the mornings, and that was no where to be found in Italy.

We then headed to the cutest town of Montepulciano to explore and shop for a few hours before lunch at Osteria Acquacheta. It was amazing! A four course meal with wine pairings. Such a heavy lunch, but some of the best food we ate!

The Best Lamb Chops


Wine Caves

All The Meats & Cheeses

Then we headed to Montalcino to walk off lunch and explore. I would skip this town next time. It was smaller and not as interesting at Montepulciano, plus during mid day most shops close down from like 1-4pm, and that is when we were there.

Next we were headed to Tenute Silvio Nardi Winery where they make the famous Brunello wine. We got a tour, tasted wine, and they actually prepared a private dinner for us. It was like we were dining in their home, and it was so neat.

The Winery

We didn’t get back to the resort until after midnight, which made for a really long day, especially for me!


Day 3: Florence

I didn’t get up for breakfast, as I was really sick today! The group departed around 10am for the 75 min drive to Florence, but I couldn’t stomach getting back on that bus and missed the whole day in Florence.

Ryan loved it, and all the history! The group went on a 5 hour tour, that I knew I wouldn’t be able to do, so I stayed behind, napped and ordered great room service. Ryan’s only complaint was that he wished they had more free time in the city to shop at the amazing stores and explore on their own.

The Duomo

Santa Maria Novella Square

I ended up taking a private car and meeting up with the group in Florence for dinner. We ate at Vincatno in the Santa Maria Novella Square. To be honest, this was one of the worst meals we had. I thought it was just because I wasn’t feeling well, but others in our group felt the same way. They did have plenty of limoncello to make up for it though. After dinner our driver took us to the top of Florence so we could see the entire city all lit up at night. It was magical!



Day 4: Siena

We laid low at the resort all morning, and Ryan had a massage and got a good workout in. Then around 1pm had a driver take us to Siena, which was only about a 20 minute drive for us. This was my favorite day in Tuscany!

Siena was amazing! We got dropped off in the center at Piazza del Campo. We shared a panini and gelato and walked around to all the shops. We ended up at the Duomo in Siena and toured inside. It was gorgeous! Then ended up at a butcher shop where they set up a charcuterie board and all the wine right in the street for us! Such a cool day!

Piazza del Campo

Duomo in Siena

Duomo in Siena

Duomo in Siena


We ended with dinner back at the resort, and it was great, just like every meal we had there.


Of everywhere we visited in Tuscany, Siena was my favorite!


Day 5: Rome

Our driver met us early, at 6am and drove us the three hours to our hotel in Rome today. We arrived around 9am and the room was ready! This was the first part of the trip where we were on our own and no longer with the group from Ryan’s work.

Hotel: Hotel Nerva

To be honest I wouldn’t stay here again. Our room was tiny and the bathroom was even tinier! I don’t think I even got in the shower (we were only in Rome for 22 hours). It was pretty noisy too, but heard that is common in Rome, think NYC. The pros though: awesome location, staff were so accommodating, and everything was clean.

We dropped off our bags and headed straight to the Colosseum. We purchased our tickets the day before with Roma Pass. There is an app you pull up on your phone and show people in a tent right outside of the Colosseum (don’t forget your ID). This is the way to go! You get to skip the long line and you can ride the bus around Rome for free that day. The Colosseum was so amazing! We didn’t do a guided tour, but you can hear all the tours around you, and get bits of information. Afterwards I went down for a quick nap to recharge and Ryan went to a local gym, where people were lifting dumbbells while smoking cigarettes!

The Colosseum

Inside The Colosseum

We then had a quick lunch outdoors and walked everywhere trying to see everything we could during our short stay…the Spanish Steps, Trevi Fountain, etc. Right near the Spanish Steps are streets of amazing shopping, think Rodeo Drive meets 5th Ave. I even got spoiled at Cartier : ) I think we walked 11 miles that day, and cooled off with all the gelato. We freshened up for dinner and wow, this might have been the best meal of the trip from the ambiance to the food! We ate at a place called Sciue, Sciue. It was a cool, short walk too, where people, mostly young professionals, were outside of bars just drinking and listening to music.

Lunch at Osteria Maracuja

Trevi Fountain

Gelato in Rome

Dinner in Rome

Days 6 – 10 : Positano

We had to get up super early to grab a cab to the train station (only about a mile away) and catch our 7am train. The only issue was all the roads were closed because of the Rome Marathon that morning. However, our hotel helped us navigate an uphill path with all our luggage to meet a cab driver who was waiting for us. I purchased the ItaliaRail tickets beforehand and this was actually a breeze! The train station was easy to navigate and the train ride was relaxing. We sat first class and were given newspapers, food and drink, and in a short 90 minutes were in Salerno!

Once in Salerno we had a short walk from the train station, across the street, to catch our ferry. I purchased ferry tickets ahead of time through Ok Ferry. The ferry ride was gorgeous along the Amalfi Coast, and lasted about 70 minutes. I’m so happy we got to arrive in Positano this way instead of by car. (You can also get a car once you get to Salerno, if you don’t want to take a ferry. It cost quite a bit more, but will take you right to your hotel in Positano.)

View Of The Amalfi Coast From The Ferry

However, once we got off at the dock, we had a .6 mile walk with luggage up a million steps and hills to the hotel! We should have hopped on the bus or got a cab but lesson learned!

Hotel: Hotel Marincanto 

This hotel was gorgeous, views, views, views! The room was pretty basic, but large and clean and with a balcony overlooking the ocean. The food and service were amazing! I would stay here again for sure!!

Our Beach Hangout!

Hotel Marincanto

Our Balcony


We spent the next few days relaxing, eating, and exploring the area.

The Beach in Positano

Streets of Flowers, So Pretty!


Favorite Restaurants: Casa E Bottega, Terrazza Cele (hotel restaurant), Restorante Max, Bruno Restaurant

Best Spaghetti at Bruno’s


Breakfast at Casa E Bottega

Casa E Bottega

Caprese Salad

We also attempted climbing the 1800 stairs to get the Path of Gods. I wasn’t feeling good that day though and it was annoying how I would have to keep stopping to catch my breath, so about 700 steps in we turned back. Next time though, next time! We were also going to take a boat to Capri, but the day we had that planned it was storming and the water was so rough that boats were not running. Also I would love to take a cooking class next time we visit.

Start Of Our Hike

Positano Views

The last morning we got a car to the Naples airport. Traffic was pretty awful, and the ride was so hilly. It took about 2.5 hours to get to the airport. We caught our flight and had a layover in Germany and then another in Chicago, and we were finally home!


I think if we were to redo this trip we would separate the two trips (Tuscany and then Rome/Positano). We already decided we want to go back and spend 2-3 days in Rome. It was the coolest city, and we didn’t even get to see half of it. I would love to go back and see the Vatican. Then we would spend another 3-4 days relaxing in Positano and get to visit Capri for a day trip and rent a boat, etc.

I don’t think I would go back to Tuscany. I am glad we went, but I think we saw and did most everything we wanted to, and I don’t need to see it again. So just kind of my feedback on the trip and what I would do if we redid it (which hopefully we will, when I’m not pregnant : ) I also have heard amazing things about Lake Como, but again, would have to be a separate trip as it’s way north.

If I could only go back to one place, hmm…I think it would be Rome! I think Ryan would say the same.

If you have any questions or want more details on things we did, restaurants, transportation, etc. just let me know!


Leave a Reply

Your email address will not be published. Required fields are marked *


Instagram did not return a 200.

Follow Me!